Dicarboxylic acid derivatives

The dicarboxylic acid derivatives according to the invention have the following structure ##STR1## wherein X denotes O, S, (CF.sub.2).sub.m, C(CF.sub.3).sub.2 or CF.sub.2 --CF(CF.sub.3) (m=1 to 10), and R stems from the following compounds: fluoro- or trifluoromethyl- and nitro- or cyanophenols, thiophenols or -aminobenzenes, 4-hydroxy-, 4-mercapto- or 4-aminocoumarins, N-hydroxysuccinimides or N-hydroxymaleimides, 2-hydroxy- or 2-mercaptobenzoxazoles or -benzothiazoles and 1-hydroxy- or 1-mercaptobenzotriazoles.

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Claims

1. A process for making a dicarboxylic acid compound having the structure: ##STR10## wherein X=O,S, (CF.sub.2).sub.m, C(CF.sub.3).sub.2 or CF.sub.2 --CF(CF.sub.3), and

m=1 to 10;
R is ##STR11## wherein D is O, S or NH, and
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 are independently H, F, CH.sub.3 or CF.sub.3 with the proviso that at least one of groups R.sup.1 to R.sup.5 is F or CF.sub.3 and at the most two of groups R.sup.1 to R.sup.5 are CH.sub.3 or CF.sub.3; ##STR12## where D is O, S or NH, and
R.sup.6, R.sup.7 are independently H, F, CH.sub.3, CF.sub.3, CN or NO.sub.2 with the proviso that at least one of groups R.sup.6 and R.sup.7 is CN or NO.sub.2; ##STR13## wherein D is O, S or NH, and
R.sup.1, R.sup.2, R.sup.3, R.sup.4 are independently H, F, CH.sub.3 or CF.sub.3, with the proviso that at the most two of groups R.sup.1 to R.sup.4 are CH.sub.3 or CF.sub.3; ##STR14## wherein R.sup.1 and R.sup.2 are independently H, F, CH.sub.3 or CF.sub.3; ##STR15## wherein Z=O or S, and
R.sup.1, R.sup.2, R.sup.3, R.sup.4 are independently H, F, CH.sub.3 or CF.sub.3 with the proviso that at the most two of groups R.sup.1 to R.sup.4 are CH.sub.3 or CF.sub.3, comprising reacting a dicarboxylic acid having the structure ##STR16## with a compound having the structure

2. The process according to claim 1, wherein the reaction is carried out in the presence of dicyclohexylcarbodiimide.

3. A process for making poly-o-hydroxyamides and poly-o-mercaptoamides comprising reacting a dicarboxylic acid compound with a bis-o-aminophenol or bis-o-aminothiophenol, said dicarboxylic acid compound having the structure: ##STR17## wherein X=O,S, (CF.sub.2).sub.m, C(CF.sub.3).sub.2 or CF.sub.2 --CF(CF.sub.3), and m=1 to 10;

R is ##STR18## wherein D is O, S or NH, and
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 are independently H, F, CH.sub.3 or CF.sub.3 with the proviso that at least one of groups R.sup.1 to R.sup.5 is F or CF.sub.3 and at the most two of groups R.sup.1 to R.sup.5 are CH.sub.3 or CF.sub.3; ##STR19## where D is O, S or NH, and
R.sup.6, R.sup.7 are independently H, F, CH.sub.3, CF.sub.3, CN or NO.sub.2 with the proviso that at least one of groups R.sup.6 and R.sup.7 is CN or NO.sub.2; ##STR20## wherein D is O, S or NH, and
R.sup.1, R.sup.2, R.sup.3, R.sup.4 are independently H, F, CH.sub.3 or CF.sub.3, with the proviso that at the most two of groups R.sup.1 to R.sup.4 are CH.sub.3 or CF.sub.3; ##STR21## wherein R.sup.1 and R.sup.2 are independently H, F, CH.sub.3 or CF.sub.3; ##STR22## wherein Z=O or S, and
R.sup.1, R.sup.2, R.sup.3, R.sup.4 are independently H, F, CH.sub.3 or CF.sub.3 with the proviso that at the most two of groups R.sup.1 to R.sup.4 are CH.sub.3 or CF.sub.3.
Referenced Cited
U.S. Patent Documents
4331592 May 25, 1982 Wissmann et al.
4339521 July 13, 1982 Ahne et al.
4622285 November 11, 1986 Ahne
4849051 July 18, 1989 Ahne et al.
5021320 June 4, 1991 Mueller et al.
5037720 August 6, 1991 Khanna
5096999 March 17, 1992 Hellmut et al.
5194568 March 16, 1993 Gregory et al.
5219981 June 15, 1993 Gregory et al.
Foreign Patent Documents
0 391 196 October 1990 EPX
1393740 May 1975 GBX
Other references
  • Labadie, et al., "Recent Advances in High Temperature Polymers For Microelectronic Applications", SAMPE Journal, vol. 25, No. 6, Nov./Dec. 1989 pp. 18-23. Soane, David S. et al., "Polymers in Microelectronics Fundamentals and Applications," Elesevier, 1989, pp. 77-124. Rutter, Edward W., et al., "A Photodefinable Benzocyclobutene Resin for Thin Film Microelectronic Applications," Proceedings of the 1992 International Conference on Multichip Modules, Apr. 1-3, 1992, pp. 394-400. Mercer F. W., "Aromatic Polyther imide oxadiazoles," High Performance Polymers, vol. 4, No. 2, 1992 pp. 73-80. Ahne, Hellmut, "Recent Advances in Photosensitive Polyamides," Polymers for Advanced Technologies, vol. 4, Oct. 1992, pp. 217-233. Katsarava, R.D. et al., "Synthesis of Polyamides using Activated bis-N-Oxysuccinimide Esters of Dicarboxylic Acids," Polymer Science U.S.S.R., vol. 26, No. 7, 1984, pp. 1668-1678. Konig, Wolfgang, et al., "N-Hydroxyverbindungen als Katalysatoren fur die Aminolyse aktivierter Ester," Chem. Ber., 106, (1973) pp. 3626-3635. Chemical Abstracts, vol. 82 (1975), No. 58354c. Chemical Abstracts, vol. 83 (1975), No. 43323p. Chemical Abstracts, vol. 84 (1976), No. 151032x. Chemical Abstracts, vol. 92 (1980), No. 181056r. Chemical Abstracts, vol. 92 (1980), No. 215344a. Advanced Organic Chemistry, Jerry March; Second Ed., McGraw-Hill Book Co., pp. 364, 376, 384 and 388 (1977).
Patent History
Patent number: 5750711
Type: Grant
Filed: Aug 28, 1996
Date of Patent: May 12, 1998
Assignee: Siemens Aktiengesellschaft (Munchen)
Inventors: Racai Sezi (Rottenbach), Hellmut Ahne (Rottenbach), Eberhard Kuehn (Hemhofen)
Primary Examiner: Johann Richter
Assistant Examiner: Jane C. Oswecki
Law Firm: Kenyon & Kenyon
Application Number: 8/704,213